Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(4-fluoro-2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497395Notes

Reaction equation

HRID 1497395 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=2)[C:3]=1[F:13].[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>CS(C)=O.[Cu]I>[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][N:24]([C:2]3[CH:10]=[CH:9][C:8]4[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=4)[C:3]=3[F:13])[C:23](=[O:27])[CH:22]=2)=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 1177986775-bromo-4-fluoro-2,3-dimethyl-2H-indazole

Product 1

HCID 1177986504-[(4-chlorobenzyl)oxy]-1-(4-fluoro-2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 2.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 5-bromo-4-fluoro-2,3-dimethyl-2H-indazole (142 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (138 mg) and potassium carbonate (242 mg) in DMSO (3 ml) were added copper(I) iodide (111 mg) and N,N′-dimethylethylenediamine (103 mg) at room temperature, and the mixture was reacted at 150° C. for 1 hr under microwave irradiation. The reaction mixture was added to 28% aqueous ammonia, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate to give the title compound (6.8 mg).

Workup

  1. customthe mixture was reacted at 150° C. for 1 hr under microwave irradiation
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-88204a8a23684bb08b31dc2cf81da260
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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